Skip to main content
Group Guided Walking Holidays

Guided walking tours & holidays

Our guided walking holidays are perfect for people who want to experience an escorted tour in a small group of like-minded people. On our tours, share cheerful moments with new friends, stroll together through beautiful countryside admiring the landscape, and cap off days enjoying a glass of luscious local wine over dinner.

Whether travelling alone, as a couple or with friends, everyone is welcome on our walking tours. There are plenty of opportunities to socialise with group members, as well as your expert guide. All are based locally and are either Headwater employees or local partners - and all are passionate about their homelands and committed to sharing their experiences with you. That way, you experience a refined, hand-picked and high-quality walking holiday with every detail expertly taken care of.

And importantly, we keep our group sizes small - typically four to 16 people. This gives our guided walking tours a good mix of travellers while giving everyone the opportunity to benefit first-hand from our guides' local knowledge. This also lets us use smaller, hand-picked guest houses, which is not possible with larger groups.

View our guided walking holidays in the UK and beyond below. If you have any questions, don't hesitate to get in touch, and be sure to check out our blog.

Average customer rating 4.9 / 5(144 verified reviews)

  • Y0751

Hotel-to-hotel guided walking holidays

Often, the best guided walking is located further afield than your hotel - and, to experience everything that's great about your chosen destination, you need to move between hotels.

On these escorted walking holidays, resident Headwater guides and local partners look after every detail of your tour. They provide comfortable transport and move your bags between hotels for you - each is hand-picked to give you an authentic flavour of the region in which you're staying, from the sweeping mountains of Montenegro or intoxicating Annapurna foothills in Nepal to the ancient Kumano Kodo Trail in Japan.

River Coa

What our travellers say

“Everything ran smoothly on travel days. Hotel was fantastic. headwater walking app was great and easy to use. ”
Mr Warne
“Excellent, professional and friendly advice when booking. The adviser worked very hard to re-arrange dates and accommodation when she found that the accommodation for our first choice dates was fully booked. Information was clear on-line. Advised clearly about costings and refunds awarded. Advice about app provide on-line Advice on contacting a guide available. Guide professional, personable, provided very useful information and advice. ”
Mr Balmer
“Booking this trip was very easy and the staff in the office were extremely helpful. The accommodation was good and the luggage transfer was efficient. ”
A Valued Customer
“Good service and good communication plus walks were very enjoyable. ”
A Valued Customer
“Everything went according to plan Taxis all on time and transfers very efficent Well chosen routes and excellent app ”
Mrs Grimes
“Excellent holiday ”
Ms Hughes
Item 1 of 1